Maybe it's location, but I've transplanted both with no failure - to the point that I'm now shaded by 3 large hollies and 2 huge cedars. I moved a couple of small seedlings from Bardstown in central KY to my home in W KY, and I swear they didn't miss a beat though there is a zone or two of climate difference. I got a lot of the root, but really didn't pay a lot of attention to how much. They were only about a foot or two tall. I made all these changes in late fall, so that might have made a difference. Our winters might be much wetter than Dave's, too, and allowed them to acclimate through several months without torture. Or maybe it was because they were so tiny to begin with.
Same with the hollies, but I only moved them from one place to the other within my own yard. If I were you, Gin, I'd wait till it's cooler before trying, but it surely is worth trying, I think.